Patent GB-716553-A (GB)
Title: Improvements in or relating to n-thiotrichloromethyl compounds
Inventor: KITTLESON ALLEN RICHARD
IPC: A01N47/04
Filed: 1951-06-19
Abstract: The invention comprises the following compounds: <FORM:0716553/IV (b)/1> where X is -CO- or -SO2- and R1 and R2 are organic residues (which may be joined) attached via carbon atoms; <FORM:0716553/IV (b)/2> where X is -CO- and Y is -SO2-, R being an organic residue attached via carbon atoms; <FORM:0716553/IV (b)/3> where R completes a 5-membered ring containing an additional hetero atom; and <FORM:0716553/IV (b)/4> where X and Y are terminal carbon atoms of the same 5-membered chain which may include an oxygen, nitrogen or sulphur atom.  The invention also includes the preparation of the above by reacting perchloromethyl mercaptan with the appropriate nitrogen compound or alkali metal salt thereof, preferably in a liquid medium such as aqueous alkali.  The invention further includes an improved process of making the above compounds and those of the parent Specification by carrying out the reaction in an aqueous medium containing a neutral water-soluble salt, preferably a salt of the same metal that has been used to form the salt of the nitrogen compound; sodium or potassium chloride is suitable.  Preferred compounds are type (1), where R1 is aromatic and R2 is a hydrocarbon or halogenated hydrocarbon group; (2) where R1 is aromatic; (3) where the 5-membered ring is that of a hydantoin, oxazolidinedione or thiazolidinedione; and (4) of the formula <FORM:0716553/IV (b)/5> where X is O, S or -CHY- and the Y symbols represent hydrogen, halogen or alkyl.  Full details are given of the procedures for making the compounds.  Examples show the preparation of the following: 3-trichloromethylthio-5-methyl - 5 - ethyl - oxazolidine - 2 : 4 - dione, N - trichloromethylthio - N - phenyl - benzenesulphonamide, 1 - nitro - 3 - trichloromethylthio - 5 : 5 - dimethylhydantoin, 3 - trichloromethylthio - thiazolidine - 2 : 4 - dione, N - trichloromethylthio - saccharin, N - trichloromethylthiomorpholine, N-trichloromethylthio-acetanilide and N - trichloromethylthio - diacetamide.  Other products mentioned are the N-trichloromethylthio derivatives of 5 : 5-dimethyl-oxazolidine-2 : 4-dione, 5 : 5-pentamethylene-oxazolidine - 2 : 4 - dione, 5 - phenyl - 5 - methyl - oxazolidine - 2 : 4 - dione, 5 - isobutyl - 5 - methyl - oxazolidine - 2 : 4 - dione, 5 - cyclopropyl - 5 - methyl - oxazolidine - 2 : 4 - dione, N - butyl - benzenesulphonamide, 5 : 5 - dimethylhydantoin and 1-acetyl-5 : 5-dimethylhydantoin.ALSO:Fungicidal, insecticidal, parasiticidal and germicidal compositions comprise one of the following types of compounds together with a diluent in intimate admixture therewith:- (1) <FORM:0716553/VI/1> where X is -CO- or -SO2- and R1 and R2 are organic radicals (which may be joined) attached via carbon atoms; (2) <FORM:0716553/VI/2> where X is -CO- and Y is -SO2-, R being an organic residue attached via carbon atoms; (3) <FORM:0716553/VI/3> where R completes a 5-membered ring containing an additional hetero atom; and (4) <FORM:0716553/VI/4> where X and Y are terminal carbon atoms of the same 5-membered chain which may include an oxygen, nitrogen or sulphur atom.  The compounds may be applied in various ways, e.g. (1) powdered and applied as undiluted dust or mixed with a solid carrier such as clay, talc or bentonite; (2) as a solution in acetone, ethanol, benzene, naphtha or other solvent or (3) dispersed in water, preferably with an anionic or non-ionic wetting agent. They may be mixed with hormones, herbicides, fertilizers or other parasiticides such as arsenates, fluorides, rotenone, DDT or benzene hexachloride.  Figures are given of the results obtained with the following compounds:-  3-trichloromethylthio-5 : 5-dimethyl-oxazolidine-2 : 4-dione and the corresponding 5-methyl-5-ethyl, 5-methyl-5-isobutyl, 5-methyl-5-cyclopropyl, 5-methyl-5-phenyl and 5 : 5- pentamethylene compounds, N - trichloromethylthio - morpholine, 3-trichloromethylthio-thiazolidine - 2 : 4 - dione, N-trichloromethylthiosaccharin, N-trichloromethylthio-N-butylbenzene-sulphonamide, N-trichloromethylthio-N-phenyl-benzenesulphonamide, 3-trichloromethylthio-5 : 5-dimethylhydantoin and its 1-nitro and 1-acetyl derivatives.  Other suitable compounds are mentioned.